Chem 345zimmerman-exam2-keyFall 06

Chem 345zimmerman-exam2-keyFall 06 - 3 fins[’93 In,rs s...

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Unformatted text preview: 3 fins: [’93) In; '-) ,rs s ’1 Organic Chemistry 345 Name (Please Write Clearly) Fall 2006 Exam 2a :2 k4? V CO “1041‘ Student ID Father's First Name_(as in UW Records) Your Seat Number Question Points Grader’s Initials '1 £— _ 2 2.0 3' 20 _”L_ s._°L___ .‘( 01 a 10 ”1 __ u . _‘1_ _ 12 ~ '1 __ 13 L! _ '7‘ )S’ L) «hm 10“.) cho- caP'@ 100 (2 Points for each Synthetic Question and 4 Points for each Mechanism Question) The Blank Last Page is for Scratch Use. Nothing on that Page will be graded. Pg2 Organic Chemistry 345 Fall 2006 Exam 2a h’e Name (Please Write Clearly) 1. Give the products of synthesis as isolated after workup. O ‘O O a) Cyclohexanone+Diethyl Oxalate W 057‘ b) Acetophenone + MezNH + CH2=O HCI FL fi’CHg‘QHL"A/Mep 6 .c) _ . _ _p-Me—Ph-fi-NH2 NaOCI f—Mgpk NH» O ‘ Cl \ d) _. 6: Q55 N CuCI k/ [8*~ Br _ C004 e) D-GUIOSC ._——.—> D11. HNO3 9 00H- _ NHCCH3I- "1+2. . , ”C,“ ”(f NeeJ€o( f) DiIHCI, A $7! (CH3 g 1 J SOZNHZI ‘ 014“” 0H Mezc-OOH g) I H+ 0 . . l (:0on h) Diethyl Adipate ——-> it; + Mac-4° NaOEt 1)LDA i) Methyl Propionate . . 2) Benzyl Bromide- \ . _ _ — CHJL j) Ph-N—C—O MeNH2 PL‘NH‘E’NHMQ' 6 Organic Chemistry 345 Fall 2006 Exam 2a Pg3 m ' Name (Please Write Clearly) 2. Give the products of synthesis as isolated after workup (Fischer Projection format is ok) a) b) c)- e.“ w D-Glucose —> ' H —Q-°H J Ho-‘Q'H HCN,NaCN ,F + {E C - 1) NaOEt CH - -CH -COOEt —> .. ’0‘ .— 3 c“) 2 2) EH CH3 3 C1 00°51] 61 O . o N 1.Benzy| Bromide [ in “of “1681(4) ii 2. H20 workup (5 cat? (£1 @7305: —> Fix-5 02:11 Me; MezNH bH' Benzoquinone- W / CHZ/CH=CH-CH3 n 2 H / _ 0H —————»A f?“ .. - :CH C9 PhCHz-NMCZ m Ibk CHAgDMcs I + - - - = = __U;c_-:.O Ph E N N N benzene A an . O . CH3CH2 HCHg 0045 CI‘IL-CHdgflL _ 150 ° _+;fMe30H- _ C 01" - ‘AmSOIe W @ '\" CH3“: Pg4 Organic Chemistry 345 Fall 2006 Exam 2a K Name (Please Write Clearly) 3. Give the products of synthesis as isolated after workup (Fischer Projection format is ok) OHLQH , Our u‘nffe,“ a) D-Erythrose NTH4+ F . (:1ng ' H 0H b) Ph-g-CHz-g-CHa 1) 2 KNH2, qu NH3 . { a. O O 2) Benzyl Bromide ’0 )1 ”,Q,‘cH‘-_%~U :C'l'lgPh. - a o . o 1 F ' S It . C) o-Cresol M, . . i.e. 0(803)2N=0 ' o (:1) Sq 1)BuLi Q Y 2) Benzyl Bromide E—t craft, Et I 00H e) D-Arabinose —> Dil. HNO3 00H- Me . I ME. Mg ‘ f) KNH2,Liq.NH3 \ NH». Cl NHL 000R 9-) _ H3 D Erythrose W F; 7 (EH;- h) Ethyl Butyrate Ql+3014zflt_%'cH'£°°E‘L NaOEt b E _ _ . i) PhCOOEt + CH3c001sé—-> (MC/310%. WW- 6:9! NaOEt min!“ - y ' ' CH=CH * j) (I;H2/ 2 CI'lL’fiw‘c‘H—IL A _ . CHZ\CIIH=CH2 *designates CH1 «CH1, isotopic carbon Page 5 Organic Chemistry 345 Fall 2006 Exam 2a Key .. . Name (Please Wr1te Clearly) Number the following in order of Increasing basicity (1 Least basic, 4 Most basic) 4' CH3CHZCH2F _Lf_, Ethoxide l ,Ethyl Acetate Enolate ;,LDA _3_ .‘ 5.- Which is least basic: Aniline, prNitroaniline, Cyclohexylamine ? p—ngfl )HJIVIL Which is most basic of the above three T’MM- 6- If you treat a racemic amine with an optically active acid, what will result' Is a set of 4 gage-Mower: e(nantiomers, diastereomers). Enantiomers have M1 (the same different) physical properties while diastereomers 'have (the at; Ewe/wt same,different) physical properties. 9L 7. Draw the chair form of @D-Glucopyranose. This needs to be drawing carefully using the skeleton below: _ H- C fie H [+0 I II _ ' [+5 * +1 0 . H H 9H 8, Using the same three -dirnensional approach as in the preceding question, draw one of the anomeric products of the reaction of D-mannose with Methanol (and HCl as a catalyst). O €44sz ‘ 9 D—MannOSe _ H 6 O ' MeOH, HCl 0H cam l \L o H . ‘7’“ . I H Q/ H c .. H 01112, 10. A compound is known to be either alpha-D-Glucopyranose or Methyl alpha-D-Glucopyranoside and gives a positive test with Tollens Reagent. The test shows that it is 00—0 CD \‘WUC-- 11. Semibullvalene undergoes a rapid degenerate Cope rearrangement, The net result is that this C8H8 hydrocarbon shows only 3 NMR peaks. Draw the reaction in three- dimensions: @s"@ Page 6 Organic Chemistry 345 Fall 2006 Exam 2Ia Kc Name (Please Write Clearly) mm «MWC K. Ffi§lk gFgwchfitx5°k $512. Draw the mechanism for the Birch Reduction o§//nisole: or“. 0W .. MM, ”9‘ yawn»: ix“ ,5 OHfifl/“i‘filfi 7:”114 um do.“ fist {M L- (H Na) «:er “(-14“ Igpvmsk M'Sf’YUfuszr 0’? 0'0“ 13 Give the mechanism for the thermal reaction of malonic acid. 6*” H’dk 15:, 35 J's ' c Clix.) H “—3 + “K (2’0” cy‘sxcg" \cf‘g '—~> H'O-l "" . 1+0: H50, 14. Give the mechanism of the Curtius reaction of benzoyl azide 6 ® - - ,m PL‘Q’EM-"zm HPLQM\ ® 9% 30:10—5'J’ ' 20:5 5”, ' 6 15. What is wrong with structure A? <f:§::> Also, what Rule does it Violate? [as slouUeL 'zf’r-Lwhel‘eut fiéfwo WLM mnd-oW/ap 7115 \lm‘b’feg WU; wk. g: or “app/f flan-d1} WPCJ‘MISM 9.114% 0‘7”“? .MWCI’E "ML wwseli ' Page 7 Organic Chemistry 345 Fall 2006 Exam 2a THIS PAGE TO BE USED FOR SCRATCH — NOTHING ON THIS PAGE WILL BE GRADED ...
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